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The Blogosphere Charity Bake-off

11.02.08 3:06 PM ET

How did an obscure personal blog that hardly anyone’s ever heard of win a fundraising competition by convincing its readers to chip in $111,352?

A vow of public humiliation, for one. Blogger Sarah Bunting, who describes her blog as a “stories-about-my-Roomba-chasing-my-cats kind of thing,” promised her readers that if they raised at least $100,000, she’d visit the landmarks of Washington, D.C., while dressed in a tomato outfit and upload video of the self-guided tour. “They know I’ll always do some stupid stunt to make the goal,” Bunting said.

The best explanation for Tomato Nation’s success could be described as “the Oprah Effect.”

Friday ended the monthlong annual “Blogger Challenge” on DonorsChoose.org, and once again, Bunting’s tiny blog, Tomato Nation, crushed the competition’s Goliaths. Bunting said she doesn’t want to brag, but “the next blog down in the general interest category raised $7,500 or something.” She also beat her own record of $108,000, which won her the competition last year.

Bunting herself helped initiate the annual Blogger Challenge four years ago on DonorsChoose.org, a site launched in spring 2000 by philanthropist Charles Best, a former social studies teacher at a Bronx public high school.

Here’s how the website works: Teachers can post requests for school supplies—anything from 35 copies of
Johnny Tremain to a pair of box turtles for the classroom aquarium—and people can fund those requests directly. “These are teachers in high-poverty areas who are spending their own money on paper and pencils,” says Best. The model is wildly effective: In the eight years since the site launched, it’s raised $25 million.

The idea for a Donors Choose “Blogger Challenge” came to Bunting in 2004, right after the “No Child Left Behind” president was reelected. Bunting, a 35-year-old Brooklyn writer, found on the website a teacher’s request for a copy of George Orwell’s
1984. It seemed like an apt metaphor, so she asked her blog’s readers to fund the request. Within two weeks, they’d funded that request
and several others to the tune of $25,000.

It was at this moment that Bunting and Best saw how blogs could extend the reach of the Donors Choose charity, and started up the annual competition that now hauls in millions every October.

Many of the competitors have huge readerships: fun-stuff aggregator
BoingBoing.net; technology superblogs
TechCrunch and
Engadget; and venture capitalist Fred Wilson’s blog,
A VC, which won the technology category of the challenge last year, raising $18,538.

“This is the future of philanthropy,” said Wilson, who knows a thing or two about raising cash. “I have been committed to doing everything I can do (within reason) to put the rubber-chicken circuit out of business. What Obama has shown, and Dean before him, is that the Internet is the most powerful fundraising tool ever invented, and we have to harness it to do more and do better.”

But Tomato Nation’s Bunting, perhaps more than most of her competitors, goes above and beyond to get her readers to pony up. “I produced a video with a Don LaFontaine-like voiceover with pictures of the Lincoln Memorial and people drinking out of ‘I Love You This Much’ coffee mugs, and the voiceover said, ‘Our once proud nation has lost its way, but the Tomato Nation is here to help!’ I had bumper stickers made up that had flag graphics and ‘Tomato Nation’ instead of a candidate’s name.”

But the most intriguing explanation for Bunting’s success is what Best calls “the Oprah Effect”: one person’s ability to passionately engage an audience of strangers, then employ this engagement to rally them to a pet cause. Best says the Blogger Challenge’s roster of competitors “includes the top 20 blogs in the world, but it’s often blogs like Tomato Nation, which don’t have an incredibly huge readership but do have an incredibly engaged relationship with their readers, that do the best.”

During a period when most charities are suffering, the competition this year attracted twice as many participants as last year. Sweetening the deal was the prize Best secured for the winner: lunch with Jerry Yang, founder of Yahoo!

“Last year I gave the prize to one of my readers,” said Bunting. “I think I might take it myself this year, though.”

Will Doig is the Features Editor at The Daily Beast. He has written for New York, The Advocate, Out, Black Book and Highlights for Children.